Chem. J. Chinese Universities

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Preparation of (R)-(+)-1,1'-Binaphthyl-2,2'-diamine Polymer as a Novel Chiral Stationary Phase by Surface-initiated Polymerization and Chromatographic Evaluation

YAO Na1,2, SONG Rui-Juan1,2, FU Yu1,2, SHI Hong-Yu1,2, LONG Yuan-De1*, HUANG Tian-Bao1   

    1. Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China;
    2. Graduate School of the Chinese Academy of Sciences, Beijing 100049, China
  • Received:2007-11-20 Revised:1900-01-01 Online:2008-06-10 Published:2008-06-10
  • Contact: LONG Yuan-De

Abstract: A novel brush-type chiral stationary phase(CSP-a) for HPLC was prepared by surface-initiated polymerization with (R)-(+)-1,1'-binaphthyl-2,2'-diamine as a chiral monomer and dichloride of 4,4'-azobis-4-cyanopentanoic acid bonded on the surface of silica gel as a radical initiator. The resolutions of the enantiomers of binaphthol derivatives, N-3,5-dinitrobenzoyl-D,L-amino acid methyl esters and isopropyl esters, and a trans-ethylene oxide derivative on CSP-a were carried out using heptane-alcohol-organic modifier-organic acid as the mobile phases under the detection conditions of the column temperature of 30 ℃ and UV wavelength of 254 nm. The effects of organic modifier and organic acid on the resolutions of the analytes on CSP-a were examined. The results show that CSP-a prepared was effective for the resolutions of the enantiomers of π-acid and π-base derivatives. Trifluoroacetic acid was a better organic modifier than acetic acid. Adding CH2Cl2 and CHCl3 to the mobile phase could increase retention and resolution of the samples on CSP-a.

Key words: Chiral stationary phase, 1,1’-Binaphthyl-2,2’-diamine, Enantiomeric resolution, Binaphthol derivative, DNB-amino acid ester, Ethylene oxide derivative

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